


Way Number Five

by BroodingSoul



Series: All the Ways Derek Made Stiles Feel Beautiful [2]
Category: Teen Wolf (TV)
Genre: First Time, Loss of Virginity, M/M, Plot What Plot/Porn Without Plot, i guess, kind of?
Language: English
Status: Completed
Published: 2014-02-06
Updated: 2014-02-06
Packaged: 2018-01-11 09:08:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,229
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1171271
Author URL: https://archiveofourown.org/users/BroodingSoul/pseuds/BroodingSoul
Summary: <blockquote class="userstuff">
              <p>Stiles and Derek have been dating for awhile.  Stiles decides he's ready for his first time, but he's a little insecure about, well, everything.</p>
            </blockquote>





	Way Number Five

**Author's Note:**

> I wrote this before I wrote "Way Number One" and I got tired of sitting on it, so I guess i'm jumping around with Derek making Stiles feel beautiful.

Stiles and Derek are tangled together on Derek's couch.  They've been making out for the past hour.  Hands have groped, skin has been caressed, hips have grinded together.  Everything feels hot; their shirts are pulled up and the feel of Stiles’ skin on Derek’s is like fire.  Usually by this time one or the other has called it a good time and they've stopped, but at the present moment there's no end in sight.

Stiles lies on his back, his legs wrapped around Derek's waist.  Derek is propped up on his elbows above him.  They kiss feverishly, frantically, almost needfully.  Stiles gasps as Derek raises a bruise on his collarbone with his teeth, tiny little nips he then soothes over with his tongue.

"Stiles?" Derek implores, murmuring into Stiles' ear and teasing his earlobe with his tongue.  His scruff scrapes the crook of Stiles’ neck, rubbing the skin raw, and Stiles can't get enough of it. 

"Yes, please," Stiles answers throatily, before the question is asked.  Derek pulls back, green eyes blazing.

"Yes?" he confirms.  Stiles nods.  "Hold on," Derek instructs.  Stiles wraps his arms around Derek's neck and tightens his legs around Derek's waist.  Derek lifts him into the air, much to Stiles' delight.  They keep kissing as Derek stumbles his way to his bed, kneeling onto it and carefully setting Stiles down.  Stiles unscissors his legs from around Derek’s waist and scoots away from Derek on the bed, suddenly bashful.  Derek raises a questioning eyebrow.

"I need to--I mean, can I use the bathroom real quick?" Stiles asks.  Derek nods and Stiles scampers to the bathroom just off of the bedroom.

Derek rummages through his bedside table, finding condoms and lube, and sets them out.  He sits idly at the foot of the bed drumming his thigh with his fingers before standing and pulling his shirt off, tossing it on the floor.  In the bathroom he hears the toilet flush and the sink turn on, so he quickly sits back on the edge of the bed.

The door opens and Stiles peeks out.  He's still wearing his t-shirt and jeans.  He notices that Derek has taken his shirt off and pulls nervously at the hem of his own shirt, not moving from the doorframe.

"Do you need to use the bathroom?" he asks Derek.  Derek's eyebrows scrunch into uncertainty, but he plays along.

"Sure," he says.  He stands and strides over, stopping hesitantly in front of Stiles.  He leans down and kisses Stiles, his lips imploring, like he’s asking Stiles why he’s acting so weird.  Stiles returns the kiss, his hands on Derek's chest, then pushes away.

"Go ahead," Stiles says.  Derek blinks, beyond confusion, but complies.  He steps into the bathroom and shuts the door.  He doesn't have to go, doesn't know why he's in the bathroom at all.  He contemplates brushing his teeth; maybe Stiles was trying to tell him his breath smelled bad.  He opts for a quick swish of mouthwash, spits, and rinses the sink.  He splashes some cold water on his face and dries off before turning off the light and heading back into the bedroom.

Stiles is laying in bed, his head propped up on pillows, the grey sheets of Derek's bed pulled up to his chin.  HIs clothes rest on top of Derek's dresser, folded neatly.  Derek can't take it anymore.

"Stiles, what's going on?" he asks, a hint of exasperation in his voice as he crosses his arms over his chest.

"I'm a virgin," Stiles replies quietly, unable to look in Derek's direction.

"I know," Derek replies.  "We've talked about it before.  I told you we would wait until you're ready."  Silence.  "Are you ready?"  Stiles nods.  "Then what is it?"

Stiles pulls the sheets up higher, mumbling his answer into them, knowing full well that Derek's wolf hearing is going to pick up the words anyway.

"No one has ever seen me naked before."

"And?"  Derek blinks, caught off guard.  Stiles pulls the sheets away from his mouth and finally looks at Derek.  Derek has never seen such a look of vulnerability from Stiles before, not even in the midst of battle when Stiles' humanity was his biggest weakness.  He unfolds his arms, shocked.

"And look at you."  His gaze wanders over Derek's shoulders, his arms, his chest, before meeting Derek's eyes.  Stiles quickly looks away, his eyes wet.

Derek's breath catches in his throat.  Never in a million years did he ever imagine Stiles--always so cocky, always with that brash confidence that Derek would never admit he coveted--would feel insecure about his body.  He doesn't bother telling Stiles that his own body comes with a wolfy price; instead he slowly crosses toward the bed and sits down on the edge.

"Stiles."  Stiles sniffs, still not looking at Derek.  "Stiles, please."  A second hangs in the air, and Stiles finally turns to look at Derek.  Derek smiles softly and reaches out, placing a palm on Stiles' neck.  Stiles closes his eyes, nuzzles into Derek's hand.  Derek's thumb caresses Stiles' left cheek, rubbing over the mole near the corner of his mouth.  Derek leans over and kisses it, his lips falling half on Stiles' cheek, half on Stiles' mouth.

"May I?" Derek whispers, fingering the sheets tucked under Stiles' chin.  Stiles' brow pulls into a look of worry, his eyes still closed.  He nods, imperceptibly, and releases his grip on the sheets.

Derek slowly pulls the sheet down the way he's seen Stiles pull off bandages.  He just wants Stiles to feel comfortable.  Inch by inch, Stiles' body is revealed.  Derek stops the sheet at Stiles' waist and takes in his boyfriend's body.

Stiles' skin is smooth and white, tinged with pink, like the inside of a seashell.  A smattering of moles spreads across his torso.  He's thin, but not frail, toned but not defined.  He looks untouched, belying the emotional scars Derek knows he must have.

Derek breathes in, audibly.  Stiles tenses, his stomach contracting, his eyes still closed.

"I know, I know.  I'm all scrawny and gangly and awkward and rubbery and--I'm like Gumby.  I'm white Gumby.  It's--"

"No."  Derek breathes out, cutting Stiles off.  He lays his hand on Stiles' chest, over his heart.  Stiles twitches.  Derek can feel Stiles' heart thumping, beating out tiny little earthquakes underneath his ribcage.  His hand trails down Stiles' side, fingers feather light, raising goosebumps on Stiles' skin.  He leans over and places a series of kisses on Stiles' stomach, touching over each mole he can find.  By the time he kisses the last one, Stiles' breathing is rapid and shallow.

Derek shifts his weight, pulling himself onto the bed and propping himself up on one elbow next to Stiles.  He traces his hand back up Stiles' side, to his neck, to his cheek.

"Stiles."  Stiles' eyelids flutter open, pupils dilated with lust and uncertainty.  Derek kisses him softly.  "You're beautiful," he whispers into Stiles' lips.  Stiles inhales suddenly, exhales slowly.

"Beautiful," Stiles repeats, unsure.  His hand glides up the curve of Derek's arm as Derek's fingers stroke down the middle of his chest.

"Magnificent," Derek murmurs, his thumb dipping into Stiles' belly button.

"Magnificent," Stiles repeats, his voice stronger.  He pulls himself up to Derek and kisses his neck.

"Exquisite," Derek whispers into Stiles' ear as his hands travel underneath the sheet, skimming the length of Stiles' ever-hardening cock.  Stiles grips Derek's hair in his hand, hips bucking at the sensation.  He kicks the sheets off and fumbles at Derek’s waist, nimble fingers trying to work the button of Derek’s jeans.

"Derek," Stiles keens plaintively.  "Yes.  Please, yes."  Derek pulls his jeans off, black boxer briefs barely concealing his erection.  Derek discards his underwear, too.

"Yes," Stiles hisses.  Derek kneels on the bed, knees between Stiles' thighs, pushing them apart.  He kisses Stiles' throat, his chest, his stomach, traveling lower.  His tongue flicks over the head of Stiles' cock.

"Derek," Stiles whimpers.  Derek relents, engulfing Stiles' cock in one swift movement.

"Yes," Stiles moans, the word a rustle on his lips.  His fists grip the sheets as he finally gives himself over.

Stiles tastes amazing, like salt and innocence.  His hips buck up until Derek’s hands clasp them firmly and keep them pinned to the bed.  Stiles whines—actually _whines_ —and Derek can’t help but smile around Stiles’ cock at this beautiful boy who still complains about not getting his way, even in the middle of a blowjob.

Stiles’ fingers tangle themselves in Derek’s hair as Derek deepthroats Stiles.  Derek hums appreciatively and the vibrations of his voice on Stiles’ cock cause the boy to moan, low and raspy.  Derek pulls off, his tongue trailing up the shaft.  Stiles’ cock hits his belly with an obscene slap.

“Derek?” Stiles questions breathlessly.  Derek smiles reassuringly before placing his hands under Stiles’ knees, lifting his legs up and pushing them toward Stiles.  Stiles breath hitches, knowing what comes next.

Derek’s head dips down and he lazily drags his tongue across Stiles’ exposed hole.

“Oh my _God_ ,” Stiles gasps, his entire body twitching with pleasure.  Derek continues the languorous path of his tongue.  He stops occasionally to rub his cheek on Stiles’ ass, his scruff scraping Stiles’ skin.  Stiles’ fists at the sheets, trying to find something to hold onto.

Derek returns to Stiles’ hole, his tongue slowly pushing in.  Stiles grips the sheets tighter as he mewls at the sensation.  Derek stays where he is, slowly tongue-fucking Stiles’ asshole, absolutely relishing every sound uttered from Stiles’ mouth, each moan and gasp making Derek’s erection throb.

“Derek, please,” Stiles groans.  He pushes back onto Derek’s tongue.  Derek pulls back and slides his tongue from Stiles’ asshole, over his balls, and all the way up to the head of Stiles’ cock.

“Please what?” Derek asks, his tongue lapping at the pre-cum leaking out of Stiles’ cock.

Stiles whimpers.  “Please _fuck me_.”

Derek smiles and carefully lowers Stiles’ legs to the bed.  He grabs the lube from the nightstand and squeezes a generous dollop onto his fingers.  Laying down next to Stiles, Derek reaches down and swirls the lube around Stiles’ asshole, before slowly pushing in his middle finger.  He’s met with some resistance as Stiles hisses.

“Do you want me to stop?” Derek asks.  Stiles shakes his head no.  Derek lets his finger slide out, and pushes in again.  “Relax,” he murmurs into Stiles’ ear, licking his earlobe and catching it with his teeth.  “Breathe out.  Kiss me.”

Stiles pulls Derek’s mouth onto his own and kisses him plaintively, his tongue searching Derek’s mouth.  Derek kisses him back as he slides his finger in and out of Stiles’ hole, the kissing distracting Stiles enough to help him relax.  Derek adds a second finger and a twist of his wrist as he continues to finger Stiles.  Stiles grinds down onto Derek’s fingers, trying to pull them in further.  Derek adds a third finger and Stiles tosses his head back, his eyes rolling up.

“ _Derek_ ,” Stiles demands.  Derek slips his fingers out of Stiles, who gasps at the sensation.  He reaches to the nightstand, grabs the condom, and puts it in Stiles hand.

“Put it on for me?” Derek asks, kissing down the line of Stiles’ jaw.  Stiles rips the condom open and tosses the wrapper on the floor.  Getting to his knees, he grasps Derek’s cock with one hand, the heat from his palm spreading down Derek’s shaft.  Stiles leans down and tentatively licks a pearl of pre-cum leaking out of Derek’s cockhead.  Derek gasps with pleasure at the feel of Stiles’ tongue rasping over the sensitive skin.  Stiles’ eyes light up and he tries a second lick, a third, a fourth, as if he’s teasing Derek.

Finally Stiles pulls back.  "Sometime, not now but sometime, you're going to have to let me do all the things you just did to me, because holy shit," Stiles babbles. He rolls the condom down and gives Derek's sheathed cock a few strokes before looking up. 

"How should I...?" Stiles trails off, and the lustful look that had been on his face is replaced by one of uncertainty. Derek feels a surge of emotions, remembering his own first time, everything fumbly and awkward and a little painful. He wants to make sure that no matter what happens in the future, Stiles will never look back on this moment with anything resembling regret or recrimination.

"C'mere," Derek murmurs. Stiles leans down and Derek kisses him softly, while maneuvering Stiles' legs so he's straddling Derek. Derek's erection twitches with his pulse, beating out an erratic rhythm on Stiles' ass.  Derek grabs the bottle of lube.

"Give me your hand," Derek tells Stiles, and squeezes lube into it. Instinctively, Stiles teaches around and coats Derek's cock with the lube. "Put some on yourself too," Derek instructs, and Stiles does, slipping two fingers into himself and groaning.  Derek could watch Stiles do that all day. 

"Are you ready?" Derek asks Stiles. Stiles nods breathlessly, his eyes regaining a glassy sheen.  Derek grabs Stiles' hand and guides it to Derek's cock. Stiles positions himself so that Derek's cock nudges his hole. 

"Now what?" Stiles asks. Derek pulls his hand away. 

"Go for it."  Stiles arches an eyebrow. "It'll be easier for you if you control it. That's why you're on top."  Stiles nods.  His hand still guiding Derek's cock, he slowly leans back.

Derek can't take his eyes off of Stiles, watching the way the flush creeps up his face, spotty at first on his cheeks, and then filling in everywhere else.  Watching his eyelids flutter shut, the way his lips draw back into a hiss as the head of Derek's cock pushes past his sphincter.

Stiles pauses and lets out the breath he didn't realize he was holding. Derek reaches up and touches Stiles everywhere but his cock. He runs his hand down Stiles' taut stomach, massages thighs, reaches up and runs his thumb over Stiles' lips. 

Stiles inhales again and as he exhales, he slowly lowers himself down.  It's tight and warm and Derek wants to close his eyes, but the way Stiles' mouth forms a perfect "o" is amazing, the way the hiss of pain turns into a whimper of pleasure and Stiles’ face softens, the crease of worry on his forehead melting away, his mouth going slack. Derek wishes he could touch Stiles everywhere at once but settles for gripping Stiles' hips.

Stiles bottoms out, his ass flush against Derek’s pelvis.  He sits there, not moving.  “It’s in,” he whispers, almost in awe, his eyes still closed and a half-smile spreading across his face.

“How does it feel?” Derek asks, running his hands up and down Stiles’ thighs.  “Describe it to me.  Tell me everything.”

“Full,” Stiles says almost immediately.  His eyebrows turn up quizzically.  “And…tingly?  Tight.”  He squeezes the muscles in his ass unexpectedly and Derek grunts at the pressure.  Stiles’ eyes fly open, the look of worry returning.  “Did I hurt you?”

“No, no, no,” Derek reassures him.  “It felt good.  _You_ feel good.”  He reaches up and pulls Stiles down to kiss him.  The motion of Stiles bending over causes Derek’s cock to slide out a bit and Stiles moans into Derek’s mouth.  Derek rolls his hips up, slowly sliding himself back in, and Stiles collapses on Derek’s chest, his mouth slack against Derek’s throat.

“Fuuuuuck,” Stiles groans, barely articulating the word.  Derek’s hands find Stiles’ ass and squeezes, pulling Stiles off of his cock and then setting him back down.  Stiles murmurs incoherently against Derek’s neck.  He retaliates by nipping at the spot behind Derek’s ear, the spot that drives Derek crazy.

Derek gasps and his hips buck up, driving his cock farther into Stiles’ ass.  Stiles squeals loudly into Derek’s ear.

“You okay?” Derek asks, worried that he’s hurt Stiles.

“So okay, so, so okay.”  Stiles slides his head up to kiss Derek.  “More like that, okay?” he mumbles into Derek’s mouth.

“Okay,” Derek replies.  He pushes Stiles back, sliding his cock up to the hilt.  Before Stiles can start riding him, Derek sits up, wraps one arm around Stiles, and flips them over on the bed so that Stiles’ is on his back, Derek’s cock never leaving Stiles’ ass.  Stiles makes a series of noises that Derek couldn’t describe if he tried.

Positioned over Stiles, propped up on his hands, Derek begins to piston his hips, maintaining a slow and steady rhythm into and out of Stiles.  Stiles mouth falls slack and he ceases to form words; the only sound coming out of him is his ragged breath, matching the pace of Derek’s thrust.

Derek wants to close his eyes and enjoy the feel of Stiles wrapped around him, but watching Stiles enjoy himself makes Derek feel better than anything he could feel or has ever felt before.  He quickens his pace and when he occasionally rolls his hips, Stiles tosses his head back and whimpers.  Derek drops down, covering Stiles’ body with his own.  The friction of his abs against Stiles’ cock causes Stiles to keen.  His hands scrabble at Derek’s back and for the first time, Derek is disappointed that Stiles chews his fingernails down to the nub, because he would gladly wear scratch marks from Stiles with pride.

Derek can feel his orgasm building and he wants to let go, but he wants Stiles to cum first.  Propping himself back up on his hands, Derek reaches down and grabs Stiles’ cock, giving it a tug.

“Derek,” Stiles whimpers.  “Don’t, I’m gonna…”

“It’s okay,” Derek assures him, dipping his head down and kissing Stiles under his jaw.

That and one more stroke are all it takes for Stiles to let go.  He cums with a shout, spraying his chest and his belly, the force of his orgasm turning his face a deep red.  He continues to grunt and moan through his orgasm, and Derek is positive that watching the corners of Stiles’ mouth twitch upward into a smile as he cums is the single most beautiful thing he’s ever seen.

The muscles of Stiles’ ass constricting with his orgasm send Derek over the edge.  He thrusts into Stiles and grunts and moans through his orgasm, vaguely aware of Stiles’ hands on his ass, trying to pull him in farther.

When they are finished, Derek pulls out of Stiles and tosses the condom on the floor, not caring where it lands.  He collapses on top of Stiles, their bodies slick with cum and sweat.  Derek breathes heavily, trying to regain his composure.  Stiles' jaw is slack, his face flush with pleasure, his eyes bright.

He huffs, a tiny laugh.  Another huff.  It grows into a low throaty chuckle.

"What?" Derek asks lazily, his body heavy on top of Stiles.

"I'm not a virgin anymore."  Derek smiles, turns his head, kisses Stiles' neck.

"I love you, beautiful boy," he sighs into Stiles' ear.  He senses Stiles' pulse quicken.

"Beautiful?" Stiles questions, his voice indignant.  Derek lifts himself to look at Stiles quizzically, only to discover an impish grin spread across his boyfriend's face.  "What happened to exquisite?" he demands.

Derek rolls his eyes and laughs.  Stiles pushes Derek's body off of him and onto his back.  He straddles Derek's hips, his torso fully exposed, any trace of insecurity gone.

"Round two?" he requests.  Derek just grins.

"Yes."

**Author's Note:**

> Have any other ideas for how Derek makes Stiles feel beautiful? Let me know!


End file.
